KR20230092095A - Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display device - Google Patents

Abstract

It relates to a compound for an organic optoelectronic device represented by Formula 1, a composition for an organic optoelectronic device including the compound, an organic optoelectronic device, and a display device.
The contents of Chemical Formula 1 are as defined in the specification.

Description

Compounds for organic optoelectronic devices, compositions for organic optoelectronic devices, organic optoelectronic devices and display devices

It relates to compounds for organic optoelectronic devices, compositions for organic optoelectronic devices, organic optoelectronic devices, and display devices.

An organic optoelectronic diode is a device capable of converting between electrical energy and light energy.

Organic optoelectronic devices can be largely divided into two types according to their operating principles. One is a photoelectric device that generates electrical energy as excitons formed by light energy are separated into electrons and holes and the electrons and holes are transferred to different electrodes, respectively. It is a light emitting device that generates light energy from

Examples of the organic optoelectronic device include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photo conductor drum.

Among them, organic light emitting diodes (OLEDs) have recently been attracting great attention due to an increase in demand for flat panel display devices. An organic light emitting device is a device that converts electrical energy into light, and the performance of the organic light emitting device is greatly affected by organic materials positioned between electrodes.

One embodiment provides a compound for an organic optoelectronic device capable of implementing a high-efficiency and long-life organic optoelectronic device.

Another embodiment provides a composition for an organic optoelectronic device including the compound for an organic optoelectronic device.

Another embodiment provides an organic optoelectronic device including the compound for an organic optoelectronic device or the composition for an organic optoelectronic device.

Another embodiment provides a display device including the organic optoelectronic device.

According to one embodiment, a compound for an organic optoelectronic device represented by Chemical Formula 1 is provided.

[Formula 1]

In Formula 1,

X ¹ and X ² are each independently O or S;

L ¹ to L ³ are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group;

Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

R ¹ to R ⁴ are each independently hydrogen, heavy hydrogen, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

According to another embodiment, a composition for an organic optoelectronic device including a first compound and a second compound is provided.

The first compound is as described above, and the second compound may be a compound for an organic optoelectronic device represented by Chemical Formula 2 below.

[Formula 2]

In Formula 2,

X ³ is O, S, NL ^a -R ^a , CR ^b R ^c or SiR ^d R ^e ;

L ^a is a single bond or a substituted or unsubstituted C6 to C12 arylene group;

R ^a , R ^b , R ^c , R ^d , R ^e , R ⁵ and R ⁶ are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group ego,

A is any one selected from the rings listed in Group II below,

[Group II]

In Group II,

* is the connection point,

X ⁴ is O or S;

R ⁷ to R ¹⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group;

At least one of R ^a and R ⁵ to R ¹⁸ is a group represented by the following formula (a),

[Formula a]

In the above formula (a),

Z ¹ to Z ³ are each independently N or CR ^f ;

at least two of Z ¹ to Z ³ are N;

R ^f is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

L ⁴ to L ⁶ are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group;

Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group,

* is a connection point.

According to another embodiment, comprising an anode and a cathode facing each other, at least one organic layer positioned between the anode and the cathode, wherein the organic layer includes the compound for an organic optoelectronic device or the composition for an organic optoelectronic device An organic optoelectronic device is provided.

According to another embodiment, a display device including the organic optoelectronic device is provided.

A high-efficiency, long-life organic optoelectronic device can be implemented.

1 is a cross-sectional view illustrating an organic light emitting device according to an exemplary embodiment.

Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, and the present invention is not limited thereby, and the present invention is only defined by the scope of the claims to be described later.

In this specification, unless otherwise defined, "substitution" means that at least one hydrogen in a substituent or compound is deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or Unsubstituted C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 A heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.

In one example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 It means substituted with a heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen of a substituent or compound is substituted with deuterium, cyano group, methyl group, ethyl group, propyl group, butyl group, phenyl group, biphenyl group, terphenyl group or naphthyl group. means it has been

In this specification, unless otherwise defined, "hetero" means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si in one functional group, and the rest being carbon. .

In the present specification, "aryl group" is a general concept of a group having one or more hydrocarbon aromatic moieties, and all elements of the hydrocarbon aromatic moiety have p-orbitals, and these p-orbitals are conjugated Forming a form, for example, including a phenyl group, a naphthyl group, etc., including a form in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, for example, a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and two or more hydrocarbon aromatic moieties may include a non-aromatic fused ring in which they are directly or indirectly fused, such as a fluorenyl group and the like.

Aryl groups include monocyclic, polycyclic or fused-ring polycyclic (ie, rings having split adjacent pairs of carbon atoms) functional groups.

In the present specification, a "heterocyclic group" is a higher concept including a heteroaryl group, and in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof, N, O, It means containing at least one heteroatom selected from the group consisting of S, P and Si. When the heterocyclic group is a fused ring, the entire heterocyclic group or each ring may include one or more heteroatoms.

For example, "heteroaryl group" means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si in the aryl group. Two or more heteroaryl groups may be directly connected through a sigma bond, or if the heteroaryl group includes two or more rings, the two or more rings may be fused to each other. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 hetero atoms.

More specifically, the substituted or unsubstituted C6 to C30 aryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthrenyl group. An unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o- Terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted benzophenanthrenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted perylenyl group, substituted or unsubstituted fluorenyl group, substituted Or an unsubstituted indenyl group, a substituted or unsubstituted furanyl group, or a combination thereof, but is not limited thereto.

More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group is a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, Substituted or unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted A substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, A substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted benzoxazinyl group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted acridinyl group, substituted or unsubstituted phenazine A substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene A group, a substituted or unsubstituted benzonaphtufuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted benzofuranofluorenyl group, a substituted or unsubstituted benzothiophenefluorenyl group, or any of these It may be a combination, but is not limited thereto.

In the present specification, the hole characteristic refers to a characteristic that can form holes by donating electrons when an electric field is applied, and has conduction characteristics along the HOMO level, so that holes formed at the anode are injected into the light emitting layer, the light emitting layer It means a property that facilitates the movement of holes formed in the anode to the anode and in the light emitting layer.

In addition, electronic properties refer to the characteristics of receiving electrons when an electric field is applied, and has conductivity along the LUMO level, so that electrons formed in the cathode are injected into the light emitting layer, electrons formed in the light emitting layer move to the cathode, and in the light emitting layer A property that facilitates movement.

Hereinafter, a compound for an organic optoelectronic device according to an embodiment will be described.

A compound for an organic optoelectronic device according to an embodiment is represented by Formula 1 below.

[Formula 1]

In Formula 1,

X ¹ and X ² are each independently O or S;

L ¹ to L ³ are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group;

Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

R ¹ to R ⁴ are each independently hydrogen, heavy hydrogen, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

The compound represented by Chemical Formula 1 is fused with dibenzofuran (or dibenzothiophene) to naphthofuran (or naphthothiophene) to increase the planarity of the molecule and improve the stacking of the lattice, thereby increasing the glass transition temperature and opening holes. Mobility is increased. In addition, hole injection and hole transfer are accelerated by substituting the amine group.

The high glass transition temperature due to these structural features maintains a stable film even against Joule heat generated during device operation, guaranteeing stable device characteristics, enabling devices with excellent lifespan to be realized, high hole mobility and fast hole The injection characteristics improve the drive voltage of the device.

For example, Chemical Formula 1 may be represented by any one of Chemical Formulas 1A, 1B, and 1C.

[Formula 1A]

[Formula 1B]

[Formula 1C]

In Formula 1A, Formula 1B, and Formula 1C,

X ¹ , X ² , L ¹ to L ³ , Ar ¹ , Ar ² and R ¹ to R ⁴ are as described above.

As a specific example, Formula 1A may be represented by any one of Formula 1A-1, Formula 1A-2, Formula 1A-3, and Formula 1A-4, depending on the specific substitution position of the amine group.

[Formula 1A-1]

[Formula 1A-2]

[Formula 1A-3]

[Formula 1A-4]

As a specific example, Formula 1B may be represented by any one of Formula 1B-1, Formula 1B-2, Formula 1B-3, and Formula 1B-4, depending on the specific substitution position of the amine group.

[Formula 1B-1]

[Formula 1B-2]

[Formula 1B-3]

[Formula 1B-4]

As a specific example, Formula 1C may be represented by any one of Formula 1C-1, Formula 1C-2, Formula 1C-3, and Formula 1C-4, depending on the specific substitution position of the amine group.

[Formula 1C-1]

[Formula 1C-2]

[Formula 1C-3]

[Formula 1C-4]

In Formulas 1A-1 to 1A-4, Formulas 1B-1 to 1B-4, and Formulas 1C-1 to 1C-4,

X ¹ , X ² , L ¹ to L ³ , Ar ¹ , Ar ² , and R ¹ to R ⁴ are as described above.

For example, Chemical Formula 1 may be represented by any one of Chemical Formulas 1A-2, 1A-3, and 1C-1 to 1C-4.

For example, Ar ¹ and Ar ² are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted anthracenyl group. group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted It may be an unsubstituted dibenzothiophenyl group or a substituted or unsubstituted dibenzosilolyl group.

As a specific example, Ar ¹ and Ar ² are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted fluorenyl group. It may be a dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.

For example, Ar ¹ and Ar ² may each independently be any one selected from substituents listed in Group I below.

[Group I]

For example, the L ¹ is a single bond,

The L ² and L ³ may each independently be a single bond or a substituted or unsubstituted phenylene group.

For example, R ¹ to R ⁴ may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

As a specific example, each of R ¹ to R ⁴ may be hydrogen.

For example, compounds for an organic optoelectronic device represented by Chemical Formula 1 may include compounds listed in Group 1 below, but are not limited thereto.

[Group 1]

[1-1] [1-2] [1-3] [1-4]

[1-5] [1-6] [1-7] [1-8]

[1-9] [1-10] [1-11] [1-12]

[1-13] [1-14] [1-15] [1-16]

[1-17] [1-18] [1-19] [1-20]

[1-21] [1-22] [1-23] [1-24]

[1-25] [1-26] [1-27] [1-28]

[1-29] [1-30] [1-31] [1-32]

[1-33] [1-34] [1-35] [1-36]

[1-37] [1-38] [1-39] [1-40]

[1-41] [1-42] [1-43] [1-44]

[1-45] [1-46] [1-47] [1-48]

[1-49] [1-50] [1-51] [1-52]

[1-53] [1-54] [1-55] [1-56]

[1-57] [1-58] [1-59] [1-60]

[1-61] [1-62] [1-63] [1-64]

[1-65] [1-66] [1-67] [1-68]

[1-69] [1-70] [1-71] [1-72]

[1-73] [1-74] [1-75] [1-76]

[1-77] [1-78] [1-79] [1-80]

[1-81] [1-82] [1-83] [1-84]

[1-85] [1-86] [1-87] [1-88]

[1-89] [1-90] [1-91] [1-92]

[1-93] [1-94] [1-95] [1-96]

[1-97] [1-98] [1-99] [1-100]

[1-101] [1-102] [1-103] [1-104]

[1-105] [1-106] [1-107] [1-108]

[1-109] [1-110] [1-111] [1-112]

[1-113] [1-114] [1-115] [1-116]

[1-117] [1-118] [1-119] [1-120]

[1-121] [1-122] [1-123] [1-124]

[1-125] [1-126] [1-127] [1-128]

[1-129] [1-130] [1-131] [1-132]

[1-133] [1-134] [1-135] [1-136]

[1-137] [1-138] [1-139] [1-140]

[1-141] [1-142] [1-143] [1-144]

[1-145] [1-146] [1-147] [1-148]

[1-149] [1-150] [1-151] [1-152]

[1-153] [1-154] [1-155] [1-156]

[1-157] [1-158] [1-159] [1-160]

[1-161] [1-162] [1-163] [1-164]

[1-165] [1-166] [1-167] [1-168]

[1-169] [1-170] [1-171] [1-172]

[1-173] [1-174] [1-175] [1-176]

[1-177] [1-178] [1-179] [1-180]

[1-181] [1-182] [1-183] [1-184]

[1-185] [1-186] [1-187] [1-188]

[1-189] [1-190] [1-191] [1-192]

[1-193] [1-194] [1-195] [1-196]

[1-197] [1-198] [1-199] [1-200]

[1-201] [1-202] [1-203] [1-204]

[1-205] [1-206] [1-207] [1-208]

[1-209] [1-210] [1-211] [1-212]

[1-213] [1-214] [1-215] [1-216]

[1-217] [1-218] [1-219] [1-220]

[1-221] [1-222] [1-223] [1-224]

[1-225] [1-226] [1-227] [1-228]

[1-229] [1-230] [1-231] [1-232]

[1-233] [1-234] [1-235] [1-236]

[1-237] [1-238] [1-239] [1-240]

[1-241] [1-242] [1-243] [1-244]

[1-245] [1-246] [1-247] [1-248]

[1-249] [1-250] [1-251] [1-252]

[1-253] [1-254] [1-255] [1-256]

[1-257] [1-258] [1-259] [1-260]

[1-261] [1-262] [1-263] [1-264]

[1-265] [1-266] [1-267] [1-268]

[1-269] [1-270] [1-271] [1-272]

[1-273] [1-274] [1-275] [1-276]

[1-277] [1-278] [1-279] [1-280]

[1-281] [1-282] [1-283] [1-284]

[1-285] [1-286] [1-287] [1-288]

[1-289] [1-290] [1-291] [1-292]

[1-293] [1-294] [1-295] [1-296]

[1-297] [1-298] [1-299] [1-300]

[1-301] [1-302] [1-303] [1-304]

[1-305] [1-306] [1-307] [1-308]

[1-309] [1-310] [1-311] [1-312]

[1-313] [1-314] [1-315] [1-316]

[1-317] [1-318] [1-319] [1-320]

[1-321] [1-322] [1-323] [1-324]

[1-325] [1-326] [1-327] [1-328]

[1-329] [1-330] [1-331] [1-332]

[1-333] [1-334] [1-335] [1-336]

[1-337] [1-338] [1-339] [1-340]

[1-341] [1-342] [1-343] [1-344]

[1-345] [1-346] [1-347] [1-348]

[1-349] [1-350] [1-351] [1-352]

[1-353] [1-354] [1-355] [1-356]

[1-357] [1-358] [1-359] [1-360]

[1-361] [1-362] [1-363] [1-364]

[1-365] [1-366] [1-367] [1-368]

[1-369] [1-370] [1-371] [1-372]

[1-373] [1-374] [1-375] [1-376]

[1-377] [1-378] [1-379] [1-380]

[1-381] [1-382] [1-383] [1-384]

[1-385] [1-386] [1-387] [1-388]

[1-389] [1-390] [1-391] [1-392]

[1-393] [1-394] [1-395] [1-396]

[1-397] [1-398] [1-399] [1-400]

[1-401] [1-402] [1-403] [1-404]

[1-405] [1-406] [1-407] [1-408]

[1-409] [1-410] [1-411] [1-412]

[1-413] [1-414] [1-415] [1-416]

[1-417] [1-418] [1-419] [1-420]

[1-421] [1-422] [1-423] [1-424]

[1-425] [1-426] [1-427] [1-428]

[1-429] [1-430] [1-431] [1-432]

[1-433] [1-434] [1-435] [1-436]

[1-437] [1-438] [1-439] [1-440]

[1-441] [1-442] [1-443] [1-444]

[1-445] [1-446] [1-447] [1-448]

[1-449] [1-450] [1-451] [1-452]

[1-453] [1-454] [1-455] [1-456]

[1-457] [1-458] [1-459] [1-460]

[1-461] [1-462] [1-463] [1-464]

[1-465] [1-466] [1-467] [1-468]

[1-469] [1-470] [1-471] [1-472]

[1-473] [1-474] [1-475] [1-476]

[1-477] [1-478] [1-479] [1-480]

[1-481] [1-482] [1-483] [1-484]

[1-485] [1-486] [1-487] [1-488]

[1-489] [1-490] [1-491] [1-492]

[1-493] [1-494] [1-495] [1-496]

[1-497] [1-498] [1-499] [1-500]

[1-501] [1-502] [1-503] [1-504]

[1-505] [1-506] [1-507] [1-508]

[1-509] [1-510] [1-511] [1-512]

[1-513] [1-514] [1-515] [1-516]

[1-517] [1-518] [1-519] [1-520]

[1-521] [1-522] [1-523] [1-524]

[1-525] [1-526] [1-527] [1-528]

[1-529] [1-530] [1-531] [1-532]

[1-533] [1-534] [1-535] [1-536]

[1-537] [1-538] [1-539] [1-540]

[1-541] [1-542] [1-543] [1-544]

[1-545] [1-546] [1-547] [1-548]

[1-549] [1-550] [1-551] [1-552]

[1-553] [1-554] [1-555] [1-556]

[1-557] [1-558] [1-559] [1-560]

[1-561] [1-562] [1-563] [1-564]

[1-565] [1-566] [1-567] [1-568]

[1-569] [1-570] [1-571] [1-572]

[1-573] [1-574] [1-575] [1-576]

[1-577] [1-578] [1-579] [1-580]

[1-581] [1-582] [1-583] [1-584]

[1-585] [1-586] [1-587] [1-588]

[1-589] [1-590] [1-591] [1-592]

[1-593] [1-594] [1-595] [1-596]

[1-597] [1-598] [1-599] [1-600]

[1-601] [1-602] [1-603] [1-604]

[1-605] [1-606] [1-607] [1-608]

[1-609] [1-610] [1-611] [1-612]

[1-613] [1-614] [1-615] [1-616]

[1-617] [1-618] [1-619] [1-620]

[1-621] [1-622] [1-623] [1-624]

[1-625] [1-626] [1-627] [1-628]

[1-629] [1-630] [1-631] [1-632]

[1-633] [1-634] [1-635] [1-636]

[1-637] [1-638] [1-639] [1-640]

[1-641] [1-642] [1-643] [1-644]

[1-645] [1-646] [1-647] [1-648]

[1-649] [1-650] [1-651] [1-652]

[1-653] [1-654] [1-655] [1-656]

[1-657] [1-658] [1-659] [1-660]

[1-661] [1-662] [1-663] [1-664]

[1-665] [1-666] [1-667] [1-668]

[1-669] [1-670] [1-671] [1-672]

[1-673] [1-674] [1-675] [1-676]

[1-677] [1-678] [1-679] [1-680]

[1-681] [1-682] [1-683] [1-684]

[1-685] [1-686] [1-687] [1-688]

[1-689] [1-690] [1-691] [1-692]

[1-693] [1-694] [1-695] [1-696]

[1-697] [1-698] [1-699] [1-700]

[1-701] [1-702] [1-703] [1-704]

[1-705] [1-706] [1-707] [1-708]

[1-709] [1-710] [1-711] [1-712]

[1-713] [1-714] [1-715] [1-716]

[1-717] [1-718] [1-719] [1-720]

[1-721] [1-722] [1-723] [1-724]

[1-725] [1-726] [1-727] [1-728]

[1-729] [1-730] [1-731] [1-732]

[1-733] [1-734] [1-735] [1-736]

[1-737] [1-738] [1-739] [1-740]

[1-741] [1-742] [1-743] [1-744]

[1-745] [1-746] [1-747] [1-748]

[1-749] [1-750] [1-751] [1-752]

[1-753] [1-754] [1-755] [1-756]

[1-757] [1-758] [1-759] [1-760]

[1-761] [1-762] [1-763] [1-764]

[1-765] [1-766] [1-767] [1-768]

A composition for an organic optoelectronic device according to another embodiment includes a first compound and a second compound, wherein the first compound is the aforementioned compound for an organic optoelectronic device, and the second compound is an organic compound represented by Chemical Formula 2 below. It may be a compound for an optoelectronic device.

[Formula 2]

In Formula 2,

X ³ is O, S, NL ^a -R ^a , CR ^b R ^c or SiR ^d R ^e ;

L ^a is a single bond or a substituted or unsubstituted C6 to C12 arylene group;

R ^a , R ^b , R ^c , R ^d , R ^e , R ⁵ and R ⁶ are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group ego,

A is any one selected from the rings listed in Group II below,

[Group II]

In Group II,

* is the connection point,

X ⁴ is O or S;

R ⁷ to R ¹⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group;

At least one of R ^a and R ⁵ to R ¹⁸ is a group represented by the following formula (a),

[Formula a]

In the above formula (a),

Z ¹ to Z ³ are each independently N or CR ^f ;

at least two of Z ¹ to Z ³ are N;

R ^f is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

L ⁴ to L ⁶ are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group;

Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group,

* is a connection point.

The second compound has a structure substituted with a nitrogen-containing 6-membered ring.

Since the second compound effectively expands the LUMO energy band by being substituted with a nitrogen-containing 6-membered ring, when used in the light emitting layer together with the first compound described above, charge mobility and stability are increased, thereby increasing the balance of holes and electrons. It is possible to improve the light emitting efficiency and lifetime characteristics of the device and lower the driving voltage.

Meanwhile, ring A of the second compound may be selected from rings listed in Group II, and for example, the second compound may be represented by any one of Formulas 2-I to 2-X.

[Formula 2-Ⅰ] [Formula 2-Ⅱ]

[Formula 2-Ⅲ] [Formula 2-IV]

[Formula 2-V] [Formula 2-VI]

[Formula 2-VII] [Formula 2-VIII]

[Formula 2-IX] [Formula 2-X]

In Formula 2-I to Formula 2-X,

X ³ , X ⁴ , Z ¹ to Z ³ , R ⁵ to R ¹⁴ , R ¹⁶ to R ¹⁸ , L ⁴ to L ⁶ , Ar ³ and Ar ⁴ are as described above.

The second compound according to an embodiment may be represented by any one of Formula 2-I, Formula 2-III, and Formula 2-VI.

The second compound according to a specific embodiment may be represented by any one of Formula 2-I-3, Formula 2-III-1, Formula 2-VI-1, and Formula 2-VI-3.

[Formula 2-Ⅰ-3] [Formula 2-Ⅲ-1]

[Formula 2-VI-1] [Formula 2-VI-3]

In Formula 2-I-3, Formula 2-III-1, Formula 2-VI-1 and Formula 2-VI-3,

X ² , Z ¹ to Z ³ , R ⁵ to R ¹¹ , L ⁴ to L ⁶ , Ar ³ and Ar ⁴ are as described above.

For example, Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthyl group. A substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilol It could be the weather.

As a specific example, Ar ³ and Ar ⁴ may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

For example, L ⁴ to L ⁶ may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

As a specific example, L ⁴ and L ⁵ may each independently represent a single bond or a substituted or unsubstituted phenylene group, and L ⁶ may represent a single bond.

For example, R ⁵ to R ¹⁸ are each independently hydrogen, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a substituted or unsubstituted C2 to C18 heterocyclic group. can

As a specific example, R ⁵ to R ¹⁸ may each independently be hydrogen, deuterium, a phenyl group, or a naphthyl group.

For example, X ³ is O, S, CR ^b R ^c or SiR ^d R ^e , and R ^b , R ^c , R ^d and R ^e are each independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted It may be a C6 to C20 aryl group.

As a specific example, R ^b , R ^c , R ^d and R ^e may each independently be a methyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

For example, the second compound may be one selected from compounds listed in Group 2 below.

[Group 2]

A composition for an organic optoelectronic device according to a more specific embodiment of the present invention includes a first compound represented by Chemical Formula 1A-2 or Chemical Formula 1A-3 and Chemical Formula 2-I-3 or Chemical Formula 2-III-1 A second compound may be included.

The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. By being included within the above range, efficiency and lifespan can be improved by implementing bipolar characteristics by setting an appropriate weight ratio using the electron transport capability of the first compound and the hole transport capability of the second compound. Within the above range, for example, it may be included in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20, for example, about 20:80 to about 70:30, about 20:80 to about 60:40, And it may be included in a weight ratio of about 30:70 to about 60:40. As a specific example, it may be included in a weight ratio of 40:60, 50:50, or 60:40.

In addition to the first compound and the second compound described above, one or more compounds may be further included.

The aforementioned compound for an organic optoelectronic device or composition for an organic optoelectronic device may be a composition that further includes a dopant.

The dopant may be, for example, a phosphorescent dopant, for example, a red, green or blue phosphorescent dopant, and may be, for example, a red or green phosphorescent dopant.

A dopant is a compound or composition for an organic optoelectronic device that is mixed in a small amount to cause light emission. In general, a material such as a metal complex that emits light by multiple excitation that excites a triplet state or higher is used. can The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one type or two or more types.

An example of the dopant may include a phosphorescent dopant, and examples of the phosphorescent dopant include Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. Organometallic compounds containing As the phosphorescent dopant, for example, a compound represented by Chemical Formula Z may be used, but is not limited thereto.

[Formula Z]

L ⁷ MX ⁵

In Formula Z, M is a metal, L ⁷ and X ⁵ are the same as or different from each other and are ligands that form a complex with M.

M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof, and L ⁷ and X ⁵ may be, for example, bi It may be a dentate ligand.

Examples of the ligand represented by L ⁷ and X ⁵ may be selected from the formulas listed in Group A below, but are not limited thereto.

[Group A]

In the group A,

R ³⁰⁰ to R ³⁰² are each independently hydrogen, deuterium, a C1 to C30 alkyl group with or without halogen substitution, a C6 to C30 aryl group with or without C1 to C30 alkyl substitution, or halogen;

R ³⁰³ to R ³²⁴ are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted Or an unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF ₅ , a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or It is a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

For example, a dopant represented by Chemical Formula III may be included.

[Formula III]

In the above formula Ⅲ,

R ¹⁰¹ to R ¹¹⁶ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR ¹³² R ¹³³ R ¹³⁴ ;

Wherein R ¹³² to R ¹³⁴ are each independently a C1 to C6 alkyl group;

At least one of R ¹⁰¹ to R ¹¹⁶ is a functional group represented by Formula III-1 below,

L ¹⁰⁰ is a bidentate ligand of a monovalent anion, and is a ligand that coordinates with iridium through an unshared electron pair of a carbon or heteroatom,

n1 and n2 are independently any one of integers from 0 to 3, n1 + n2 is any one of integers from 1 to 3,

[Formula III-1]

In Formula Ⅲ-1,

R ¹³⁵ to R ¹³⁹ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR ¹³² R ¹³³ R ¹³⁴ ;

* means a part connected to a carbon atom.

For example, a dopant represented by Chemical Formula Z-1 may be included.

[Formula Z-1]

In the above formula Z-1, rings A, B, C, and D each independently represent a 5- or 6-membered carbocyclic or heterocyclic ring;

R ^A , R ^B , R ^C , and R ^D each independently represent mono-, di-, tri-, or tetra-substituted, or unsubstituted;

L ^B , L ^C , and L ^D are each a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO ₂ , CRR', SiRR', GeRR', and combinations thereof independently selected from the group consisting of;

When nA is 1, L ^E is a group consisting of a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO ₂ , CRR', SiRR', GeRR', and combinations thereof is selected from; When nA is 0, L ^E is not present;

R ^A , R ^B , R ^C , R ^D , R , and R' are each hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, heteroalkyl group, arylalkyl group, alkoxy group, aryloxy group, amino group, silyl group, alkenyl group , Cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group independently selected from the group consisting of, and combinations thereof; any adjacent R ^A , R ^B , R ^C , R ^D , R , and R' are optionally linked to form a ring; X ^B , X ^C , X ^D , and X ^E are each independently selected from the group consisting of carbon and nitrogen; Q ¹ , Q ² , Q ³ , and Q ⁴ each represent an oxygen or a direct bond.

A dopant according to an embodiment may be a platinum complex, and may be represented by Chemical Formula IV below.

[Formula IV]

In Formula IV,

X ¹⁰⁰ is selected from O, S and NR ¹³¹ ;

R ¹¹⁷ to R ¹³¹ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or - SiR ¹³² R ¹³³ R ¹³⁴ ;

Wherein R ¹³² to R ¹³⁴ are each independently a C1 to C6 alkyl group;

At least one of R ¹¹⁷ to R ¹³¹ is -SiR ¹³² R ¹³³ R ¹³⁴ or a tert-butyl group.

The above compound for an organic optoelectronic device or composition for an organic optoelectronic device may be formed by a dry film formation method such as chemical vapor deposition.

Hereinafter, an organic optoelectronic device to which the above-described compound for an organic optoelectronic device or composition for an organic optoelectronic device is applied will be described.

The organic optoelectronic device is not particularly limited as long as it is a device capable of converting electrical energy and light energy, and examples thereof include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photoreceptor drum.

Here, an organic light emitting device, which is an example of an organic optoelectronic device, will be described with reference to drawings.

1 is a cross-sectional view showing an organic light emitting device according to an exemplary embodiment.

Referring to FIG. 1 , an organic light emitting device 100 according to an embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 positioned between the anode 120 and the cathode 110. include

The anode 120 may be made of, for example, a conductor having a high work function so as to smoothly inject holes, and may be made of, for example, metal, metal oxide, and/or conductive polymer. The anode 120 may be formed of, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, or gold or an alloy thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO and Al or SnO ₂ and Sb; conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDOT), polypyrrole, and polyaniline; It is not.

The cathode 110 may be made of, for example, a conductor having a low work function so as to facilitate electron injection, and may be made of, for example, metal, metal oxide, and/or conductive polymer. The negative electrode 110 may be formed of, for example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; Multi-layered materials such as LiF/Al, LiO ₂ /Al, LiF/Ca, LiF/Al and BaF ₂ /Ca may be mentioned, but are not limited thereto.

The organic layer 105 may include the above-described compound for an organic optoelectronic device or composition for an organic optoelectronic device.

The organic layer 105 includes the light emitting layer 130, and the light emitting layer 130 may include the above-described compound for an organic optoelectronic device or composition for an organic optoelectronic device.

The composition for an organic optoelectronic device further comprising a dopant may be, for example, a green light emitting composition.

The light emitting layer 130 may include, for example, the above-described compound for an organic optoelectronic device or composition for an organic optoelectronic device as a phosphorescent host.

The organic layer may further include a charge transport region in addition to the light emitting layer.

The charge transport region may be, for example, the hole transport region 140 .

The hole transport region 140 may further increase hole injection and/or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.

Specifically, the hole transport region 140 may include a hole transport layer between the anode 120 and the light emitting layer 130, and a hole transport auxiliary layer between the light emitting layer 130 and the hole transport layer. At least one of the listed compounds may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[Group B]

In addition to the above compounds, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A and similar structures may be used for the hole transport region 140.

Also, the charge transport region may be, for example, the electron transport region 150 .

The electron transport region 150 may further increase electron injection and/or electron mobility between the cathode 110 and the light emitting layer 130 and block holes.

Specifically, the electron transport region 150 may include an electron transport layer between the cathode 110 and the light emitting layer 130, and an electron transport auxiliary layer between the light emitting layer 130 and the electron transport layer. At least one of the listed compounds may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[Group C]

One embodiment may be an organic light emitting device including a light emitting layer as an organic layer.

Another embodiment may be an organic light emitting device including a light emitting layer and a hole transport region as an organic layer.

Another embodiment may be an organic light emitting device including an emission layer and an electron transport region as an organic layer.

As shown in FIG. 1 , an organic light emitting device according to an exemplary embodiment of the present invention may include a hole transport region 140 and an electron transport region 150 in addition to the emission layer 130 as the organic layer 105 .

Meanwhile, the organic light emitting device may further include an electron injection layer (not shown), a hole injection layer (not shown), and the like in addition to the light emitting layer as the organic layer described above.

In the organic light emitting device 100, after forming an anode or a cathode on a substrate, an organic layer is formed by a dry film method such as evaporation, sputtering, plasma plating, or ion plating, and then a cathode or cathode thereon. It can be manufactured by forming an anode.

The organic light emitting device described above may be applied to an organic light emitting display device.

The above-described implementation will be described in more detail through the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of rights.

Hereinafter, the starting materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry, or synthesized through known methods, unless otherwise specified.

(Preparation of compounds for organic optoelectronic devices)

Synthesis Example 1: Synthesis of Compound 1-2

[Scheme 1]

Intermediate 12-chlorobenzo[4,5]thieno[2,3-g]naphtho[2,1-b]benzofuran 5.0 g (13.93 mmol) and intermediate N-phenyl-[1,1'-biphenyl]-4-amine 3.42 g (13.93 mmol), 2.14 g (22.29 mmol) of sodium t-butoxide, and 0.5 g (1.25 mmol) of Tri-tert-butylphosphine were dissolved in 95 ml of toluene, After adding 0.38 g (0.41 mmol) of Pd ₂ (dba) _3, the mixture was refluxed and stirred for 12 hours under a nitrogen atmosphere. After completion of the reaction, after extraction with toluene and distilled water, the organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with n-hexane/dichloromethane (2:1 volume ratio) to obtain 6.7 g of the target compound 1-2 as a white solid (yield: 85%).

Calculated: C, 84.63; H, 4.44; N, 2.47; O, 2.82; S, 5.65

Assay: C, 84.63; H, 4.44; N, 2.47; O, 2.82; S, 5.64

Synthesis Example 2: Synthesis of Compound 1-171

[Scheme 2]

The intermediate 12-chlorobenzo[4,5]thieno[2,3-g]naphtho[1,2-b]benzofuran and the intermediate N-phenyl-[1,1'-biphenyl]-4-amine were mixed in a 1:1 equivalence ratio. Compound 1-171 was synthesized in the same manner as in Synthesis Example 1 (6.5 g, yield 82%), except that it was used as .

Calculated: C, 84.63; H, 4.44; N, 2.47; O, 2.82; S, 5.65

Assay: C, 84.63; H, 4.44; N, 2.48; O, 2.82; S, 5.65

Synthesis Example 3: Synthesis of Compound 1-189

[Scheme 3]

The intermediate 12-chlorobenzo[4,5]thieno[2,3-g]naphtho[1,2-b]benzofuran and the intermediate N-(4-(naphthalen-1-yl)phenyl)-[1,1'- Compound 1-189 was synthesized in the same manner as in Synthesis Example 1, except that biphenyl]-3-amine was used in an equivalent ratio of 1:1 (7.2g, yield 74%).

Calculated: C, 86.55; H, 4.50; N, 2.02; O, 2.31; S, 4.62

Assay: C, 86.55; H, 4.50; N, 2.02; O, 2.32; S, 4.62

Synthesis Example 4: Synthesis of Compound 1-208

[Scheme 4]

The intermediate 11-chlorobenzo[4,5]thieno[2,3-g]naphtho[2,1-b]benzofuran and the intermediate 4-(naphthalen-1-yl)-N-phenylaniline were used in an equivalent ratio of 1:1. Except, Compound 1-208 was synthesized in the same manner as in Synthesis Example 1 (7.3 g, yield 85%).

Calculated: C, 85.55; H, 4.41; N, 2.27; O, 2.59; S, 5.19

Assay: C, 85.55; H, 4.41; N, 2.27; O, 2.59; S, 5.19

Synthesis Example 5: Synthesis of Compound 1-263

[Scheme 5]

The intermediate 11-chlorobenzo[4,5]thieno[2,3-g]naphtho[1,2-b]benzofuran and the intermediate 3-(naphthalen-1-yl)-N-phenylaniline were used in an equivalent ratio of 1:1. Except, compound 1-263 was synthesized in the same manner as in Synthesis Example 1 (7.1 g, yield 82%).

Calculated: C, 85.55; H, 4.41; N, 2.27; O, 2.59; S, 5.19

Assay: C, 85.55; H, 4.41; N, 2.28; O, 2.59; S, 5.19

Synthesis Example 6: Synthesis of Compound 1-283

[Scheme 6]

The intermediate 11-chlorobenzo[4,5]thieno[2,3-g]naphtho[1,2-b]benzofuran and the intermediate 4-(naphthalen-2-yl)-N-phenylaniline were used in an equivalent ratio of 1:1. Except, compound 1-283 was synthesized in the same manner as in Synthesis Example 1 (7.2 g, yield 84%).

Calculated: C, 85.55; H, 4.41; N, 2.27; O, 2.59; S, 5.19

Assay: C, 85.55; H, 4.41; N, 2.28; O, 2.59; S, 5.19

Synthesis Example 7: Synthesis of Compound 1-298

[Scheme 7]

The intermediate 10-chlorobenzo[4,5]thieno[2,3-g]naphtho[2,1-b]benzofuran and the intermediate N-phenyl-[1,1'-biphenyl]-4-amine were mixed in a 1:1 equivalence ratio. Compound 1-298 was synthesized in the same manner as in Synthesis Example 1, except that it was used as (7.0 g, yield 90%).

Calculated: C, 84.63; H, 4.44; N, 2.47; O, 2.82; S, 5.65

Assay: C, 84.63; H, 4.45; N, 2.47; O, 2.82; S, 5.65

Synthesis Example 8: Synthesis of Compound 1-162

[Scheme 8]

The intermediate 12-chlorobenzo[4,5]thieno[2,3-g]naphtho[1,2-b]benzofuran and the intermediate 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine were mixed in a 1:1 ratio. Compound 1-162 was synthesized in the same manner as in Synthesis Example 1 except that the equivalent ratio was used (7.05 g, yield 83%).

Calculated: C, 84.98; H, 4.81; N, 2.30; O, 2.63; S, 5.28

Assay: C, 84.98; H, 4.81; N, 2.30; O, 2.63; S, 5.28

Synthesis Example 9: Synthesis of Compound 1-465

[Scheme 9]

The intermediate 12-chlorobenzo[b]naphtho[2',1':4,5]thieno[2,3-e]benzofuran and the intermediate 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine were mixed with 1 Compound 1-465 was synthesized in the same manner as in Synthesis Example 1 (7.4 g, yield 87%), except that the mixture was used in an equivalent ratio of: 1.

Calculated: C, 84.98; H, 4.81; N, 2.30; O, 2.63; S, 5.27

Assay: C, 84.98; H, 4.81; N, 2.30; O, 2.63; S, 5.28

Synthesis Example 10: Synthesis of Compound 1-473

[Scheme 10]

The intermediate 12-chlorobenzo[b]naphtho[2',1':4,5]thieno[2,3-e]benzofuran and the intermediate 4-(naphthalen-1-yl)-N-phenylaniline were mixed in a 1:1 equivalence ratio. Compound 1-473 was synthesized in the same manner as in Synthesis Example 1 (7.01 g, yield 81%), except that the mixture was used.

Calculated: C, 85.55; H, 4.41; N, 2.27; O, 2.58; S, 5.19

Assay: C, 85.55; H, 4.41; N, 2.27; O, 2.59; S, 5.19

Synthesis Example 11: Synthesis of Compound 1-119

[Scheme 11]

The intermediate 12-chlorobenzo[4,5]thieno[2,3-g]naphtho[2,1-b]benzofuran and the intermediate N-(4-(naphthalen-1-yl)phenyl)naphthalen-1-amine were mixed with 1 Compound 1-119 was synthesized in the same manner as in Synthesis Example 1 (6.95 g, yield 75%), except that the ratio was 1:1.

Calculated: C, 86.33; H, 4.38; N, 2.10; O, 2.40; S, 4.80

Assay: C, 86.33; H, 4.38; N, 2.10; O, 2.40; S, 4.80

Synthesis Example 12: Synthesis of Compound 1-176

[Scheme 12]

The intermediate 12-chlorobenzo[4,5]thieno[2,3-g]naphtho[1,2-b]benzofuran and the intermediate 4-(naphthalen-1-yl)-N-phenylaniline were used in an equivalent ratio of 1:1. Except, Compound 1-176 was synthesized in the same manner as in Synthesis Example 1 (7.03 g, yield 82%).

Calculated: C, 85.55; H, 4.42; N, 2.27; O, 2.59; S, 5.19

Assay: C, 85.55; H, 4.41; N, 2.27; O, 2.59; S, 5.19

Comparative Synthesis Example 1: Synthesis of Compound H1

[Scheme 13]

The intermediate 2-chlorobenzo[b]benzo[4,5]thieno[2,3-g]benzofuran and the intermediate 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:1. Except, compound H1 was synthesized in the same manner as in Synthesis Example 1 (7.68 g, yield 85%).

Calculated: C, 83.99; H, 4.88; N, 2.51; O, 2.87; S, 5.75

Assay: C, 83.99; H, 4.88; N, 2.51; O, 2.87; S, 5.75

Comparative Synthesis Example 2: Synthesis of Compound H2

[Scheme 14]

Except for using the intermediate 2-chlorobenzo[b]benzo[4,5]thieno[2,3-g]benzofuran and the intermediate N-phenyl-[1,1'-biphenyl]-4-amine in an equivalent ratio of 1:1 Then, compound H2 was synthesized in the same manner as in Synthesis Example 1 (6.95 g, yield 83%).

Calculated: C, 83.53; H, 4.48; N, 2.71; O, 3.09; S, 6.19

Assay: C, 83.53; H, 4.48; N, 2.71; O, 3.09; S, 6.19

Comparative Synthesis Example 3: Synthesis of Compound H3

[Scheme 15]

Except for using the intermediate 3-chlorobenzo[b]benzo[4,5]thieno[2,3-g]benzofuran and the intermediate N-phenyl-[1,1'-biphenyl]-4-amine in an equivalent ratio of 1:1 Then, compound H3 was synthesized in the same manner as in Synthesis Example 1 (7.2 g, yield 86%).

Calculated: C, 83.53; H, 4.48; N, 2.71; O, 3.09; S, 6.19

Assay: C, 83.54; H, 4.48; N, 2.71; O, 3.09; S, 6.19

Comparative Synthesis Example 4: Synthesis of Compound H4

[Scheme 16]

Except for using the intermediate 3-chlorobenzo[b]benzo[4,5]thieno[2,3-g]benzofuran and the intermediate N-phenyldibenzo[b,d]furan-3-amine in an equivalent ratio of 1:1, Compound H4 was synthesized in the same manner as in Synthesis Example 1 (7.03 g, yield 82%).

Calculated: C, 81.33; H, 3.98; N, 2.63; O, 6.02; S, 6.03

Assay: C, 81.33; H, 3.98; N, 2.63; O, 6.02; S, 6.03

Comparative Synthesis Example 5: Synthesis of Compound H5

[Scheme 17]

Compound H5 was synthesized in the same manner as in Synthesis Example 1, except that the intermediate 3-chlorobenzo[b]benzo[4,5]thieno[2,3-g]benzofuran and the intermediate diphenylamine were used in an equivalent ratio of 1:1. (5.95 g, yield 83%).

Calculated: C, 81.61; H, 4.34; N, 3.17; O, 3.62; S, 7.26

Assay: C, 81.61; H, 4.34; N, 3.17; O, 3.63; S, 7.26

Synthesis Example 13: Synthesis of Compound A-6

[Scheme 18]

In a round bottom flask, add 9.39 g (25.38 mmol) of 2-chloro-4-(4-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine to 100 mL of tetrahydrofuran and 50 mL of distilled water. 2-(11,11-dimethyl-11H-benzo[a]fluoren-7-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1.0 equivalent, tetrakistriphenylphos After adding 0.03 equivalent of pin palladium and 2 equivalents of potassium carbonate, the mixture is heated to reflux under a nitrogen atmosphere. After 6 hours, the reaction solution was cooled, the water layer was removed, and the organic layer was dried under reduced pressure. After washing the obtained solid with water and hexane, the solid was recrystallized with 200 mL of toluene to obtain 10.5 g (69% yield) of Compound A-6.

Calculated: C, 87.82; H, 5.19; N, 6.98

Assay: C, 87.82; H, 5.19; N, 6.98

Synthesis Example 14: Synthesis of Compound A-14

[Scheme 19]

8.19 g of the intermediate 2,4-di ([1,1'-biphenyl] -4-yl) -6-chloro-1,3,5-triazine and the intermediate 4,4,5,5-tetramethyl-2-( Compound A-14 was synthesized in the same manner as in Synthesis Example 13, except that naphtho[1,2-b]benzofuran-7-yl)-1,3,2-dioxaborolane was used in an equivalent ratio of 1:1 ( 10.7 g, yield 75%).

Calculated: C, 85.83; H, 4.51; N, 6.98; O, 2.66

Assay: C, 85.83; H, 4.52; N, 6.98; O, 2.66

Synthesis Example 15: Synthesis of Compound A-19

[Scheme 20]

8.73 g of the intermediate 2-chloro-4- (4- (naphthalen-1-yl) phenyl) -6-phenyl-1,3,5-triazine and the intermediate 4,4,5,5-tetramethyl-2- (naphtho Compound A-19 was synthesized in the same manner as in Synthesis Example 13, except that [1,2-b]benzofuran-1-yl)-1,3,2-dioxaborolane was used in an equivalent ratio of 1:1 (9.7 g, yield 66%).

Calculated: C, 85.54; H, 4.38; N, 7.30; O, 2.78

Assay: C, 85.54; H, 4.38; N, 7.30; O, 2.78

Synthesis Example 16: Synthesis of Compound A-15

[Scheme 21]

7.93 g of the above intermediate 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine and the intermediate Except for using 4,4,5,5-tetramethyl-2-(naphtho[1,2-b]benzofuran-7-yl)-1,3,2-dioxaborolane in an equivalent ratio of 1:1, the above Synthesis Example Compound A-15 was synthesized in the same manner as in 13 (9.95 g, yield 70%).

Calculated: C, 83.87; H, 4.09; N, 6.83; O, 5.20

Assay: C, 83.88; H, 4.09; N, 6.83; O, 5.20

Synthesis Example 17: Synthesis of Compound A-17

[Scheme 22]

8.7 g of the intermediate 2-chloro-4- (4- (naphthalen-1-yl) phenyl) -6-phenyl-1,3,5-triazine and the intermediate 4,4,5,5-tetramethyl-2- (naphtho Compound A-17 was synthesized in the same manner as in Synthesis Example 13, except that [1,2-b]benzofuran-7-yl)-1,3,2-dioxaborolane was used in an equivalent ratio of 1:1 (9.43 g, yield 65%).

Calculated: C, 85.54; H, 4.38; N, 7.30; O, 2.78

Assay: C, 85.54; H, 4.38; N, 7.30; O, 2.78

(Manufacture of organic light emitting device)

Example 1

A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a plasma cleaner, cleaned for 10 minutes using oxygen plasma, and then transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as an anode, compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum deposited on an ITO substrate to form a hole injection layer having a thickness of 100 Å. Compound A was deposited thereon to a thickness of 1300 Å to form a hole transport layer. Compound 1-2 obtained in Synthesis Example 1 was deposited on top of the hole transport layer to a thickness of 700 Å to form a hole transport auxiliary layer. Compound B-1 and Compound B-2 were used as hosts on the hole transport auxiliary layer, doped with 2 wt% of [Ir(piq) ₂ acac] as a dopant, and a light emitting layer having a thickness of 400 Å was formed by vacuum deposition. Here, compound B-1 and compound B-2 were used in a weight ratio of 5:5. Subsequently, compound C was deposited on the light emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compound D and LiQ were simultaneously vacuum deposited at a weight ratio of 1: 1 to form an electron transport layer with a thickness of 300 Å. An organic light emitting device was fabricated by forming a cathode by sequentially vacuum depositing 15 Å of LiQ and 1200 Å of Al on the electron transport layer.

ITO / Compound A (3% NDP-9 doping, 100Å) / Compound A (1300Å) / Compound 1-2 (700Å) / EML [Compound B-1 / Compound B-2] (98wt%): [Ir (piq ) ₂ acac] (2wt%) (400Å) / Compound C (50Å) / Compound D: LiQ (300Å) / LiQ (15Å) / Al (1200Å).

Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

Compound B-1: 9-(3-(4-(4-(naphthalen-2-yl)phenyl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole

Compound B-2: N-([1,1'-biphenyl]-3-yl)-N-(4-(naphthalen-2-yl)phenyl)-11-phenyl-11H-benzo[a]carbazol-2 -amine

Compound C: 2-(3-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine

Compound D: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazin-2-yl)phenyl)quinoline

Examples 2 to 12 and Comparative Examples 1 to 4

As shown in Table 1 below, an organic light emitting device was manufactured in the same manner as in Example 1, except that the hole transport auxiliary layer was changed.

Example 13

A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a plasma cleaner, cleaned for 10 minutes using oxygen plasma, and then transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as an anode, compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum deposited on the ITO substrate to form a hole injection layer having a thickness of 100 Å, and the hole injection layer A hole transport layer was formed by depositing compound A on top to a thickness of 1300 Å. Compound E was deposited to a thickness of 700 Å on top of the hole transport layer to form a hole transport auxiliary layer. Compound 1-171 obtained in Synthesis Example 2 and Compound A-6 obtained in Synthesis Example 13 were simultaneously used as hosts on top of the hole transport auxiliary layer, doped with 2 wt% of [Ir(piq) ₂ acac] as a dopant, and vacuum deposited to 400 Å. A thick light emitting layer was formed. Here, compound 1-171 and compound A-6 were used in a weight ratio of 5:5. Subsequently, compound C was deposited on the light emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compound D and LiQ were simultaneously vacuum deposited at a weight ratio of 1: 1 to form an electron transport layer with a thickness of 300 Å. An organic light emitting device was fabricated by forming a cathode by sequentially vacuum depositing 15 Å of LiQ and 1200 Å of Al on the electron transport layer.

ITO / Compound A (3% NDP-9 doping, 100 Å) / Compound A (1300 Å) / Compound E (700 Å) / EML [Compound 1-171 / Compound A-6 = 5:5 w / w] (98wt% ): [Ir(piq) ₂ acac] (2wt%) (400Å) / Compound C (50Å) / Compound D: LiQ (300Å) / LiQ (15Å) / Al (1200Å).

Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

Compound E: N,N-di([1,1'-biphenyl]-4-yl)-7,7-dimethyl-7H-fluoreno[4,3-b]benzofuran-10-amine

Examples 14 to 23 and Comparative Examples 5 to 8

As shown in Table 2 below, an organic light emitting device was manufactured in the same manner as in Example 13, except that the host was changed.

evaluation

Luminous efficiencies and driving voltages of the organic light emitting devices according to Examples 1 to 23 and Comparative Examples 1 to 8 were evaluated.

The specific measurement method is as follows, and the results are shown in Tables 1 and 2.

(1) Measurement of change in current density according to voltage change

With respect to the manufactured organic light emitting device, while increasing the voltage from 0V to 10V, a current value flowing through the unit device was measured using a current-voltmeter (Keithley 2400), and the result was obtained by dividing the measured current value by the area.

(2) Measurement of luminance change according to voltage change

The result was obtained by measuring the luminance of the manufactured organic light emitting device using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V.

(3) Measurement of luminous efficiency

Luminous efficiency (cd/A) of the same current density (10 mA/cm ² ) was calculated using the luminance, current density, and voltage measured from (1) and (2) above.

Relative values based on the luminous efficiency of Comparative Example 2 were calculated and shown in Table 1 below.

Relative values based on the luminous efficiency of Comparative Example 5 were calculated and shown in Table 2 below.

(4) Driving voltage measurement

The result was obtained by measuring the driving voltage of each device at 15 mA/cm ² using a current-voltmeter (Keithley 2400).

Relative values based on the driving voltage of Comparative Example 1 are shown in Table 1 below.

Relative values based on the driving voltage of Comparative Example 7 are shown in Table 2 below.

division compound Driving voltage (%) Luminous efficiency (%) Example 1 1-2 95 106 Example 2 1-171 94 105 Example 3 1-189 94 107 Example 4 1-208 95 106 Example 5 1-263 94 106 Example 6 1-283 94 106 Example 7 1-298 95 105 Example 8 1-162 95 107 Example 9 1-465 95 105 Example 10 1-473 94 106 Example 11 1-119 94 105 Example 12 1-176 94 107 Comparative Example 1 H1 100 99 Comparative Example 2 H2 99 100 Comparative Example 3 H3 100 98 Comparative Example 4 H4 99 98

division host Luminous efficiency (%) Driving voltage (%) No. 1
host 2nd
host Example 13 1-171 A-6 106 96 Example 14 1-171 A-14 107 95 Example 15 1-162 A-6 107 96 Example 16 1-162 A-19 106 97 Example 17 1-176 A-14 107 96 Example 18 1-176 A-15 108 96 Example 19 1-176 A-17 107 95 Example 20 1-189 A-15 106 96 Example 21 1-189 A-17 106 95 Example 22 1-283 A-6 107 96 Example 23 1-283 A-14 108 96 Comparative Example 5 H1 A-6 100 99 Comparative Example 6 H2 A-15 99 101 Comparative Example 7 H3 A-17 98 100 Comparative Example 8 H4 A-15 99 102

Referring to Tables 1 and 2, it was confirmed that the luminous efficiency and driving voltage of the compound according to the present invention were improved in the single host compared to the comparative compound. In particular, referring to Table 2, even when combined with the second host, emission It can be seen that the overall efficiency and driving voltage are greatly improved.

Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements of those skilled in the art using the basic concepts of the present invention defined in the following claims also fall within the scope of the present invention. will be.

100: organic light emitting element
105 organic layer
110: cathode
120: anode
130: light emitting layer
140: hole transport region
150: electron transport area

Claims (16)

A compound for an organic optoelectronic device represented by Formula 1 below:
[Formula 1]

In Formula 1,
X ¹ and X ² are each independently O or S;
L ¹ to L ³ are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group;
Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
R ¹ to R ⁴ are each independently hydrogen, heavy hydrogen, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group. According to claim 1,
Formula 1 is a compound for an organic optoelectronic device represented by any one of Formulas 1A, 1B and 1C:
[Formula 1A]

[Formula 1B]

[Formula 1C]

In Formula 1A, Formula 1B, and Formula 1C,
X ¹ , X ² , L ¹ to L ³ , Ar ¹ , Ar ² and R ¹ to R ⁴ are as defined in claim 1. According to claim 2,
A compound for an organic optoelectronic device represented by any one of Formulas 1A-2, 1A-3, and Formulas 1C-1 to 1C-4:
[Formula 1A-2]

[Formula 1A-3]

[Formula 1C-1]

[Formula 1C-2]

[Formula 1C-3]

[Formula 1C-4]

In Formula 1A-2, Formula 1A-3, and Formula 1C-1 to Formula 1C-4,
X ¹ , X ² , L ¹ to L ³ , Ar ¹ , Ar ² , and R ¹ to R ⁴ are as defined in claim 2. According to claim 1,
Ar ¹ and Ar ² are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, Substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted A compound for an organic optoelectronic device, which is a dibenzothiophenyl group or a substituted or unsubstituted dibenzosilolyl group. According to claim 1,
Wherein Ar ¹ and Ar ² are each independently any one selected from the substituents listed in Group I, a compound for an organic optoelectronic device:
[Group I]

In Group I above, * is a connection point. According to claim 1,
L ¹ is a single bond;
Wherein L ² and L ³ are each independently a single bond or a substituted or unsubstituted phenylene group, a compound for an organic optoelectronic device. According to claim 1,
A compound for an organic optoelectronic device selected from among the compounds listed in Group 1 below:
[Group 1]
[1-1] [1-2] [1-3] [1-4]

[1-5] [1-6] [1-7] [1-8]

[1-9] [1-10] [1-11] [1-12]

[1-13] [1-14] [1-15] [1-16]

[1-17] [1-18] [1-19] [1-20]

[1-21] [1-22] [1-23] [1-24]

[1-25] [1-26] [1-27] [1-28]

[1-29] [1-30] [1-31] [1-32]

[1-33] [1-34] [1-35] [1-36]

[1-37] [1-38] [1-39] [1-40]

[1-41] [1-42] [1-43] [1-44]

[1-45] [1-46] [1-47] [1-48]

[1-49] [1-50] [1-51] [1-52]

[1-53] [1-54] [1-55] [1-56]

[1-57] [1-58] [1-59] [1-60]

[1-61] [1-62] [1-63] [1-64]

[1-65] [1-66] [1-67] [1-68]

[1-69] [1-70] [1-71] [1-72]

[1-73] [1-74] [1-75] [1-76]

[1-77] [1-78] [1-79] [1-80]

[1-81] [1-82] [1-83] [1-84]

[1-85] [1-86] [1-87] [1-88]

[1-89] [1-90] [1-91] [1-92]

[1-93] [1-94] [1-95] [1-96]

[1-97] [1-98] [1-99] [1-100]

[1-101] [1-102] [1-103] [1-104]

[1-105] [1-106] [1-107] [1-108]

[1-109] [1-110] [1-111] [1-112]

[1-113] [1-114] [1-115] [1-116]

[1-117] [1-118] [1-119] [1-120]

[1-121] [1-122] [1-123] [1-124]

[1-125] [1-126] [1-127] [1-128]

[1-129] [1-130] [1-131] [1-132]

[1-133] [1-134] [1-135] [1-136]

[1-137] [1-138] [1-139] [1-140]

[1-141] [1-142] [1-143] [1-144]

[1-145] [1-146] [1-147] [1-148]

[1-149] [1-150] [1-151] [1-152]

[1-153] [1-154] [1-155] [1-156]

[1-157] [1-158] [1-159] [1-160]

[1-161] [1-162] [1-163] [1-164]

[1-165] [1-166] [1-167] [1-168]

[1-169] [1-170] [1-171] [1-172]

[1-173] [1-174] [1-175] [1-176]

[1-177] [1-178] [1-179] [1-180]

[1-181] [1-182] [1-183] [1-184]

[1-185] [1-186] [1-187] [1-188]

[1-189] [1-190] [1-191] [1-192]

[1-193] [1-194] [1-195] [1-196]

[1-197] [1-198] [1-199] [1-200]

[1-201] [1-202] [1-203] [1-204]

[1-205] [1-206] [1-207] [1-208]

[1-209] [1-210] [1-211] [1-212]

[1-213] [1-214] [1-215] [1-216]

[1-217] [1-218] [1-219] [1-220]

[1-221] [1-222] [1-223] [1-224]

[1-225] [1-226] [1-227] [1-228]

[1-229] [1-230] [1-231] [1-232]

[1-233] [1-234] [1-235] [1-236]

[1-237] [1-238] [1-239] [1-240]

[1-241] [1-242] [1-243] [1-244]

[1-245] [1-246] [1-247] [1-248]

[1-249] [1-250] [1-251] [1-252]

[1-253] [1-254] [1-255] [1-256]

[1-257] [1-258] [1-259] [1-260]

[1-261] [1-262] [1-263] [1-264]

[1-265] [1-266] [1-267] [1-268]

[1-269] [1-270] [1-271] [1-272]

[1-273] [1-274] [1-275] [1-276]

[1-277] [1-278] [1-279] [1-280]

[1-281] [1-282] [1-283] [1-284]

[1-285] [1-286] [1-287] [1-288]

[1-289] [1-290] [1-291] [1-292]

[1-293] [1-294] [1-295] [1-296]

[1-297] [1-298] [1-299] [1-300]

[1-301] [1-302] [1-303] [1-304]

[1-305] [1-306] [1-307] [1-308]

[1-309] [1-310] [1-311] [1-312]

[1-313] [1-314] [1-315] [1-316]

[1-317] [1-318] [1-319] [1-320]

[1-321] [1-322] [1-323] [1-324]

[1-325] [1-326] [1-327] [1-328]

[1-329] [1-330] [1-331] [1-332]

[1-333] [1-334] [1-335] [1-336]

[1-337] [1-338] [1-339] [1-340]

[1-341] [1-342] [1-343] [1-344]

[1-345] [1-346] [1-347] [1-348]

[1-349] [1-350] [1-351] [1-352]

[1-353] [1-354] [1-355] [1-356]

[1-357] [1-358] [1-359] [1-360]

[1-361] [1-362] [1-363] [1-364]

[1-365] [1-366] [1-367] [1-368]

[1-369] [1-370] [1-371] [1-372]

[1-373] [1-374] [1-375] [1-376]

[1-377] [1-378] [1-379] [1-380]

[1-381] [1-382] [1-383] [1-384]

[1-385] [1-386] [1-387] [1-388]

[1-389] [1-390] [1-391] [1-392]

[1-393] [1-394] [1-395] [1-396]

[1-397] [1-398] [1-399] [1-400]

[1-401] [1-402] [1-403] [1-404]

[1-405] [1-406] [1-407] [1-408]

[1-409] [1-410] [1-411] [1-412]

[1-413] [1-414] [1-415] [1-416]

[1-417] [1-418] [1-419] [1-420]

[1-421] [1-422] [1-423] [1-424]

[1-425] [1-426] [1-427] [1-428]

[1-429] [1-430] [1-431] [1-432]

[1-433] [1-434] [1-435] [1-436]

[1-437] [1-438] [1-439] [1-440]

[1-441] [1-442] [1-443] [1-444]

[1-445] [1-446] [1-447] [1-448]

[1-449] [1-450] [1-451] [1-452]

[1-453] [1-454] [1-455] [1-456]

[1-457] [1-458] [1-459] [1-460]

[1-461] [1-462] [1-463] [1-464]

[1-465] [1-466] [1-467] [1-468]

[1-469] [1-470] [1-471] [1-472]

[1-473] [1-474] [1-475] [1-476]

[1-477] [1-478] [1-479] [1-480]

[1-481] [1-482] [1-483] [1-484]

[1-485] [1-486] [1-487] [1-488]

[1-489] [1-490] [1-491] [1-492]

[1-493] [1-494] [1-495] [1-496]

[1-497] [1-498] [1-499] [1-500]

[1-501] [1-502] [1-503] [1-504]

[1-505] [1-506] [1-507] [1-508]

[1-509] [1-510] [1-511] [1-512]

[1-513] [1-514] [1-515] [1-516]

[1-517] [1-518] [1-519] [1-520]

[1-521] [1-522] [1-523] [1-524]

[1-525] [1-526] [1-527] [1-528]

[1-529] [1-530] [1-531] [1-532]

[1-533] [1-534] [1-535] [1-536]

[1-537] [1-538] [1-539] [1-540]

[1-541] [1-542] [1-543] [1-544]

[1-545] [1-546] [1-547] [1-548]

[1-549] [1-550] [1-551] [1-552]

[1-553] [1-554] [1-555] [1-556]

[1-557] [1-558] [1-559] [1-560]

[1-561] [1-562] [1-563] [1-564]

[1-565] [1-566] [1-567] [1-568]

[1-569] [1-570] [1-571] [1-572]

[1-573] [1-574] [1-575] [1-576]

[1-577] [1-578] [1-579] [1-580]

[1-581] [1-582] [1-583] [1-584]

[1-585] [1-586] [1-587] [1-588]

[1-589] [1-590] [1-591] [1-592]

[1-593] [1-594] [1-595] [1-596]

[1-597] [1-598] [1-599] [1-600]

[1-601] [1-602] [1-603] [1-604]

[1-605] [1-606] [1-607] [1-608]

[1-609] [1-610] [1-611] [1-612]

[1-613] [1-614] [1-615] [1-616]

[1-617] [1-618] [1-619] [1-620]

[1-621] [1-622] [1-623] [1-624]

[1-625] [1-626] [1-627] [1-628]

[1-629] [1-630] [1-631] [1-632]

[1-633] [1-634] [1-635] [1-636]

[1-637] [1-638] [1-639] [1-640]

[1-641] [1-642] [1-643] [1-644]

[1-645] [1-646] [1-647] [1-648]

[1-649] [1-650] [1-651] [1-652]

[1-653] [1-654] [1-655] [1-656]

[1-657] [1-658] [1-659] [1-660]

[1-661] [1-662] [1-663] [1-664]

[1-665] [1-666] [1-667] [1-668]

[1-669] [1-670] [1-671] [1-672]

[1-673] [1-674] [1-675] [1-676]

[1-677] [1-678] [1-679] [1-680]

[1-681] [1-682] [1-683] [1-684]

[1-685] [1-686] [1-687] [1-688]

[1-689] [1-690] [1-691] [1-692]

[1-693] [1-694] [1-695] [1-696]

[1-697] [1-698] [1-699] [1-700]

[1-701] [1-702] [1-703] [1-704]

[1-705] [1-706] [1-707] [1-708]

[1-709] [1-710] [1-711] [1-712]

[1-713] [1-714] [1-715] [1-716]

[1-717] [1-718] [1-719] [1-720]

[1-721] [1-722] [1-723] [1-724]

[1-725] [1-726] [1-727] [1-728]

[1-729] [1-730] [1-731] [1-732]

[1-733] [1-734] [1-735] [1-736]

[1-737] [1-738] [1-739] [1-740]

[1-741] [1-742] [1-743] [1-744]

[1-745] [1-746] [1-747] [1-748]

[1-749] [1-750] [1-751] [1-752]

[1-753] [1-754] [1-755] [1-756]

[1-757] [1-758] [1-759] [1-760]

[1-761] [1-762] [1-763] [1-764]

[1-765] [1-766] [1-767] [1-768]

. Including a first compound and a second compound,
The first compound is a compound for an organic optoelectronic device according to claim 1,
The second compound is a compound for an organic optoelectronic device represented by Formula 2, a composition for an organic optoelectronic device:
[Formula 2]

In Formula 2,
X ³ is O, S, NL ^a -R ^a , CR ^b R ^c or SiR ^d R ^e ;
L ^a is a single bond or a substituted or unsubstituted C6 to C12 arylene group;
R ^a , R ^b , R ^c , R ^d , R ^e , R ⁵ and R ⁶ are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group ego,
A is any one selected from the rings listed in Group II below,
[Group II]

In Group II,
* is the connection point,
X ⁴ is O or S;
R ⁷ to R ¹⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group;
At least one of R ^a and R ⁵ to R ¹⁸ is a group represented by the following formula (a),
[Formula a]

In the above formula (a),
Z ¹ to Z ³ are each independently N or CR ^f ;
at least two of Z ¹ to Z ³ are N;
R ^f is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
L ⁴ to L ⁶ are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group;
Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group,
* is a connection point. According to claim 8,
Formula 2 is a composition for an organic optoelectronic device represented by any one of the following Formulas 2-I to 2-X:
[Formula 2-Ⅰ] [Formula 2-Ⅱ]

[Formula 2-Ⅲ] [Formula 2-IV]

[Formula 2-V] [Formula 2-VI]

[Formula 2-VII] [Formula 2-VIII]

[Formula 2-IX] [Formula 2-X]

In Formula 2-I to Formula 2-X,
X ³ , X ⁴ , Z ¹ to Z ³ , R ⁵ to R ¹⁴ , R ¹⁶ to R ¹⁸ , L ⁴ to L ⁶ , Ar ³ and Ar ⁴ are the same as in claim 8 . According to claim 9,
The second compound is a composition for an organic optoelectronic device represented by any one of Formula 2-I, Formula 2-III and Formula 2-VI. According to claim 8,
The second compound is a composition for an organic optoelectronic device represented by any one of Formula 2-I-3, Formula 2-III-1, Formula 2-VI-1, and Formula 2-VI-3:
[Formula 2-Ⅰ-3] [Formula 2-Ⅲ-1]

[Formula 2-VI-1] [Formula 2-VI-3]

In Formula 2-I-3, Formula 2-III-1, Formula 2-VI-1 and Formula 2-VI-3,
X ² , Z ¹ to Z ³ , R ⁵ to R ¹¹ , L ⁴ to L ⁶ , Ar ³ and Ar ⁴ are as defined in claim 8. According to claim 8,
Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, A substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group. , Compositions for organic optoelectronic devices. According to claim 8,
The second compound is a composition for an organic optoelectronic device in which one selected from the compounds listed in Group 2 below:
[Group 2]

. anode and cathode facing each other,
At least one organic layer positioned between the anode and the cathode,
The organic layer may include a compound for an organic optoelectronic device according to any one of claims 1 to 7; or
An organic optoelectronic device comprising the composition for an organic optoelectronic device according to any one of claims 8 to 13. According to claim 14,
The organic layer includes a light emitting layer,
The light-emitting layer comprises the compound for an organic optoelectronic device or the composition for an organic optoelectronic device. A display device comprising the organic optoelectronic device according to claim 14 .

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